N-(2-氯苯基)苯磺酰胺 | 21226-30-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2-氯苯基)苯磺酰胺
• 英文名称: 2-chloro-1-(benzenesulfonylamino)benzene
• 英文别名: N-(2-chlorophenyl)benzenesulfonamide；Benzolsulfonsaeure-<2-chlor-anilid>
• CAS: 21226-30-2
• 化学式: C₁₂H₁₀ClNO₂S
• mdl: MFCD00541867
• 分子量: 267.736
• InChiKey: KMSWCQQQRKBBAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  N-(2-氯苯基)苯磺酰胺 在 硝酸 作用下， 生成 N-(2-氯-4-硝基苯)苯磺酰胺
  参考文献：
  名称：

  DE157859

  摘要：

  公开号：
• 作为产物：
  描述：

  苯磺酰苯胺 在 sodium hypochlorite 作用下， 生成 N-(2-氯苯基)苯磺酰胺
  参考文献：
  名称：

  Raper; Thompson; Cohen, Journal of the Chemical Society, 1904, vol. 85, p. 377

  摘要：

  DOI：

文献信息

• N- and 2-substituted N-(phenylsulfonyl)glycines as inhibitors of rat lens aldose reductase
  作者：Jack DeRuiter、Ronald F. Borne、Charles A. Mayfield

  DOI：10.1021/jm00121a027

  日期：1989.1

  A variety of N-(phenylsulfonyl)-N-phenylglycines 5, N-(phenylsulfonyl)-2-phenylglycines 6, and N-(phenylsulfonyl)anthranilic acids 7 were prepared as analogues of the N-(phenylsulfonyl)glycine 1 aldose reductase inhibitors. In the rat lens assay, several derivatives of 5 display greater inhibitory activity than the corresponding glycines 1, suggesting that N-phenyl substitution enhances affinity for

  制备了多种N-（苯磺酰基）-N-苯基甘氨酸5，N-（苯磺酰基）-2-苯基甘氨酸6和N-（苯磺酰基）邻氨基苯甲酸7作为N-（苯磺酰基）甘氨酸1醛糖还原酶抑制剂的类似物。 。在大鼠晶状体测定中，5的几种衍生物比相应的甘氨酸1表现出更大的抑制活性，表明N-苯基取代增强了对醛糖还原酶的亲和力。5和1的4-苯甲酰氨基类似物的酶动力学评估表明，这些化合物通过相同的机理产生抑制作用。但是，系列5和系列1的化合物之间的相对抑制效能的显着差异可能表明这些化合物不会以完全相同的方式与抑制剂结合位点相互作用。对系列6的各个对映异构体的评估表明，S异构体比相应的R异构体具有更高的活性。另外，除了萘类似物6n以外，该系列的S立体异构体显示出比甘氨酸1更大的抑制能力。邻氨基苯甲酸酯7通常比甘氨酸1活性低，这表明芳族环直接掺入甘氨酸侧。链可能导致对醛糖还原酶的亲和力降低。
• A Convenient and Benign Synthesis of Sulphonamides in PEG-400
  作者：Pranab Jyoti Das、Bhaskar Sarmah

  DOI：10.14233/ajchem.2015.16853

  日期：——

  A simple and convenient method is reported for the synthesis of a series of sulphonamides in PEG-400 using potassium carbonate as the base. The reaction is carried out in a heterogeneous medium and consequently product recovery is simple. The desired products with a variety of aromatic amines could be synthesized in a short reaction time in good yield. The PEG could be recovered for reuse.

  据报道，使用碳酸钾作为碱，在PEG-400中合成一系列磺胺类化合物的方法简单便捷。反应在非均相介质中进行，因此产物回收简单。在较短的反应时间内，可以通过该方法合成带有多种芳香胺的目标产物，且产率良好。PEG可以回收重复使用。
• Sequential C–S and S–N Coupling Approach to Sulfonamides
  作者：Kai Chen、Wei Chen、Bing Han、Wanzhi Chen、Miaochang Liu、Huayue Wu

  DOI：10.1021/acs.orglett.0c00183

  日期：2020.3.6

  A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.

  描述了涉及硝基芳烃，（杂）芳基硼酸和焦亚硫酸钾的一锅三组分反应，生成磺酰胺。通过不需要金属催化剂的连续CS和SN偶联，获得了具有不同反应性官能团的多种磺酰胺，收率好至极好。
• Ortho Effect in Dissociation of Substituted N-Phenylbenzenesulfonamides
  作者：Jiří Nádvorník、Miroslav Ludwig

  DOI：10.1135/cccc20011380

  日期：——

  Twenty-five 2,2'-disubstituted N-phenylbenzenesulfonamides (2-X-C₆H₄SO₂NHC₆H₄-Y-2') were synthesised and their purity checked by elemental analysis. This set of model substrates involved all possible combinations of methoxy, methyl, hydrogen, chloro, and nitro substituents. The dissociation constants of the sulfonamides were determined by potentiometric titration in methanol, pyridine, dimethyl sulfoxide, N,N-dimethylformamide, acetone, and acetonitrile. The dissociation constants pK_HA obtained were correlated with various sets of substituent constants describing electronic and steric effects of the substituents, and the statistically treated data were used to discuss the contribution of the substituent effects in the dissociation and the difference between the effects transmitted from the two rings. A linear regression model explaining 99% of the variability of experimental data in all the solvents has been found and discussed. Moreover, the experimental data were also interpreted by the methods using latent variables, the principal component analysis (PCA) and conjugated deviation analysis (CDA), and two latent variables were shown to be statistically significant in the description of dissociation. The first obviously describes common action of electronic and steric effects of substituents; the other probably concerns a combined effect of substituent and solvent on the position of acid-base equilibrium.

  二十五种2,2'-二取代N-苯基苯磺酰胺（2-X-C6H4SO2NHC6H4-Y-2'）被合成，并通过元素分析检查其纯度。这组模型底物涉及甲氧基、甲基、氢、氯和硝基取代基的所有可能组合。苯磺酰胺的解离常数通过在甲醇、吡啶、二甲基亚砜、N,N-二甲基甲酰胺、丙酮和乙腈中的电位滴定确定。所得到的解离常数pKHA与描述取代基电子和立体效应的各种取代基常数相关联，统计处理的数据用于讨论取代基效应在解离中的贡献以及从两个环传递的效应之间的差异。已找到并讨论了一个线性回归模型，解释了在所有溶剂中实验数据变异性的99%。此外，实验数据还通过使用潜在变量的方法进行解释，主成分分析（PCA）和共轭偏差分析（CDA），并且显示两个潜在变量在描述解离中具有统计显著性。第一个明显描述了取代基的电子和立体效应的共同作用；另一个可能涉及取代基和溶剂对酸碱平衡位置的联合影响。
• Palladium-catalyzed desulfitative arylation of sulfonamides with sodium arylsulfinates
  作者：Zijian Zhao、Yan Lian、Chang Zhao、Bing Wang

  DOI：10.1080/00397911.2018.1452262

  日期：2018.6.18

  ABSTRACT A Pd(II)-catalyzed desulfitative arylation protocol between sulfonamides and sodium arylsulfinates was herein reported. The direct arylation reaction was successfully achieved by a Pd(II)/Ag(I)-mediated system without participation of any external ligands with a release of SO2. And different N-aryl sulfonamides were obtained readily in up to 86% yields, exhibiting good functional groups tolerance

  摘要本文报道了 Pd(II) 催化的磺酰胺和芳基亚磺酸钠之间的脱硫芳基化方案。直接芳基化反应是通过 Pd(II)/Ag(I) 介导的系统成功实现的，无需任何外部配体的参与并释放 SO2。不同的 N-芳基磺酰胺很容易以高达 86% 的产率获得，表现出良好的官能团耐受性（25 个例子）。图形概要

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